Sodium Hydroxide → 2-Amino-5-(propan-2-yloxy)benzoic acid

HRID 1702615Notes

Reaction equation

HRID 1702615 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:17]([O-])=O)=[C:9]([CH:16]=1)[C:10]([O:12]C(C)C)=[O:11])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[CH:1]([O:4][C:5]1[CH:16]=[C:9]([C:10]([OH:12])=[O:11])[C:8]([NH2:17])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12719170HCID 12719170, compound

Product 1

HCID 127191892-Amino-5-(propan-2-yloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

74.0 G. of 5-isopropoxy-2-nitrobenzoic acid, isopropyl ester was dissolved in 650 ml. of ethanol and 145 ml. of 4 N sodium hydroxide solution. This solution was allowed to stir at room temperature for 16 hours. The reaction mixture was diluted with 2.0 l. of water and washed three times with 1 l. of dichloromethane. The aqueous layer was then acidified to pH<2 with concentrated hydrochloric acid and extracted three times with 1.0 l. of ether. The combined ether extracts were washed with 1.0 l. of saturated brine, dried over anhydrous sodium sulfate, filtered through Celite and evaporated to an orange oil (65.9 g.) which solidified on cooling, mp 129°-131°. The above solid was dissolved in 1.0 l. of ethyl acetate and hydrogenated, using 3.1 g. of 10% palladium on carbon as catalyst. When hydrogen uptake had ceased, the catalyst was removed by filtration and the filtrate was evaporated to a yellow solid, 49.5 g. (mp 120°-122° ).

Workup

  1. additionThe reaction mixture was diluted with 2.0 l
  2. washof water and washed three times with 1 l
  3. extractionextracted three times with 1.0 l
  4. washThe combined ether extracts were washed with 1.0 l
  5. dry with materialof saturated brine, dried over anhydrous sodium sulfate
  6. filtrationfiltered through Celite
  7. customevaporated to an orange oil (65.9 g.) which
  8. temperatureon cooling
  9. dissolutionThe above solid was dissolved in 1.0 l
  10. customthe catalyst was removed by filtration
  11. customthe filtrate was evaporated to a yellow solid, 49.5 g

Sources & evidence

ORD record
ord-004028af8acc400bb7fece57ab4b6bc3
Source dataset
uspto-grants-1982_09
Patent number
US04348396

Reaction notes

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